Which airlines fly to Chicago?

Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Region of Ontario according to our data. Air Canada is the first choice among our users, with 59% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Ontario to Chicago?

Porter Airlines, Air Canada, and American Airlines are the most popular carriers operating from Ontario to Chicago

How many flights depart from Region of Ontario to Chicago on average per week?

612 flights are operational weekly from Region of Ontario to Chicago as of November 2025. The most popular departure day for this route is Thu, with 16% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Flight times from Region of Ontario to Chicago vary, but if you’re flying out of Ottawa and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 2h 08m on average. Another popular route from Region of Ontario to Chicago is flying from Hamilton to Chicago O'Hare Intl Airport, which will take roughly 8h 21m. Keep in mind that layovers or delays could extend your travel time.

How many flights depart from Region of Ontario to Chicago on average per day?

87 flights are operational daily from Region of Ontario to Chicago as of November 2025. The most popular departure time for this route is 11:00a.m., with 48% of flights per day taking off at noon.

When did momondo last update prices for flights from Ontario to Chicago?

Prices for flights from Ontario to Chicago were last updated today.

How many operators does momondo search for flights from Ontario to Chicago?

There are 5 operators available for flights from Ontario to Chicago as of November 2025.

How old do you have to be to fly from Ontario to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ontario to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

C$ 170 Cheap Flights from Ontario to Chicago in 2025/26

1 adult

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Find the cheapest flights from Ontario to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:15 a.m. - 10:05 a.m.YTZ-MDW

1h 50mdirect

4:15 p.m. - 6:57 p.m.MDW-YTZ

1h 42mdirect

C$ 251Porter Airlines

Find Deal

mar., 2 dic. - vie., 5 dic.

9:15 a.m. - 10:05 a.m.YTZ-MDW

1h 50mdirect

11:00 a.m. - 1:42 p.m.MDW-YTZ

1h 42mdirect

C$ 255Porter Airlines

Find Deal

lun., 22 dic. - lun., 5 ene.

1:47 p.m. - 6:23 p.m.YYZ-ORD

5h 36m1 stop

5:00 a.m. - 11:12 a.m.ORD-YYZ

5h 12m1 stop

C$ 257American Airlines

Find Deal

mar., 9 dic. - vie., 12 dic.

3:30 p.m. - 4:40 p.m.YYZ-ORD

2h 10mdirect

9:15 p.m. - 11:59 p.m.ORD-YYZ

1h 44mdirect

C$ 258United Airlines

Find Deal

vie., 9 ene. - dom., 18 ene.

5:30 p.m. - 6:50 p.m.YYZ-ORD

2h 20mdirect

4:50 p.m. - 7:45 p.m.ORD-YYZ

1h 55mdirect

C$ 259United Airlines

Find Deal

jue., 8 ene. - dom., 11 ene.

3:30 p.m. - 4:40 p.m.YYZ-ORD

2h 10mdirect

8:52 a.m. - 6:57 p.m.ORD-YYZ

9h 05m1 stop

C$ 264United Airlines

Find Deal

lun., 26 ene. - lun., 2 feb.

6:00 a.m. - 7:15 a.m.YYZ-ORD

2h 15mdirect

7:10 a.m. - 3:59 p.m.ORD-YYZ

7h 49m1 stop

C$ 266American Airlines

Find Deal

mar., 9 dic. - sáb., 13 dic.

9:00 p.m. - 10:05 p.m.YYZ-ORD

2h 05mdirect

6:28 p.m. - 9:21 p.m.ORD-YYZ

1h 53mdirect

C$ 268Lufthansa

Find Deal

jue., 8 ene. - dom., 11 ene.

12:05 p.m. - 1:01 p.m.YYZ-ORD

1h 56mdirect

6:05 a.m. - 11:48 a.m.ORD-YYZ

4h 43m1 stop

C$ 275Air Canada

Find Deal

jue., 8 ene. - dom., 11 ene.

7:00 a.m. - 1:01 p.m.YUL-ORD

7h 01m1 stop

12:50 p.m. - 3:57 p.m.ORD-YUL

2h 07mdirect

C$ 297Air Canada

Find Deal

jue., 26 feb. - lun., 2 mar.

American Airlines flights from Region of Ontario to Chicago

Our best American Airlines deals on Region of Ontario to Chicago flight tickets

American Airlines

9 Dec

YYZ1:47 p.m.Toronto Pearson Intl

5h 36m

1 stop

ORD6:23 p.m.Chicago O'Hare Intl

12 Dec

ORD5:00 a.m.Chicago O'Hare Intl

5h 12m

1 stop

YYZ11:12 a.m.Toronto Pearson Intl

C$ 257

Find similar

American Airlines

9 Dec

YYZ6:00 a.m.Toronto Pearson Intl

2h 15m

ORD7:15 a.m.Chicago O'Hare Intl

13 Dec

ORD7:10 a.m.Chicago O'Hare Intl

7h 49m

1 stop

YYZ3:59 p.m.Toronto Pearson Intl

C$ 266

Find similar

American Airlines

5 Apr

YYZ6:15 a.m.Toronto Pearson Intl

2h 15m

ORD7:30 a.m.Chicago O'Hare Intl

8 Apr

ORD4:59 p.m.Chicago O'Hare Intl

5h 06m

1 stop

YYZ11:05 p.m.Toronto Pearson Intl

C$ 271

Find similar

Air Canada flights from Region of Ontario to Chicago

Our best Air Canada deals on Region of Ontario to Chicago flight tickets

Air Canada

8 Jan

YYZ12:05 p.m.Toronto Pearson Intl

1h 56m

ORD1:01 p.m.Chicago O'Hare Intl

11 Jan

ORD6:05 a.m.Chicago O'Hare Intl

4h 43m

1 stop

YYZ11:48 a.m.Toronto Pearson Intl

C$ 275

Find similar

Air Canada

12 Dec

YYZ2:15 p.m.Toronto Pearson Intl

1h 55m

ORD3:10 p.m.Chicago O'Hare Intl

15 Dec

ORD8:15 p.m.Chicago O'Hare Intl

1h 39m

YYZ10:54 p.m.Toronto Pearson Intl

C$ 280

Find similar

Air Canada

4 Dec

YYZ6:20 a.m.Toronto Pearson Intl

5h 58m

1 stop

ORD11:18 a.m.Chicago O'Hare Intl

7 Dec

ORD8:00 a.m.Chicago O'Hare Intl

1h 40m

YYZ10:40 a.m.Toronto Pearson Intl

C$ 289

Find similar

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 2/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

vie. 5/12

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 251

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

lun. 22/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

lun. 5/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 255

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mar. 9/12

1:47 p.m.-6:23 p.m.

1 stop5h 36m

Chicago O'Hare Intl

vie. 12/12

5:00 a.m.-11:12 a.m.

1 stop5h 12m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 9/1

3:30 p.m.-4:40 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

dom. 18/1

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 8/1

5:30 p.m.-6:50 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

dom. 11/1

4:50 p.m.-7:45 p.m.

Nonstop1h 55m

C$ 259

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

lun. 26/1

3:30 p.m.-4:40 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

lun. 2/2

8:52 a.m.-6:57 p.m.

1 stop9h 05m

C$ 264

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mar. 9/12

6:00 a.m.-7:15 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

sáb. 13/12

7:10 a.m.-3:59 p.m.

1 stop7h 49m

C$ 266

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 8/1

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

dom. 11/1

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 268

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 8/1

12:05 p.m.-1:01 p.m.

Nonstop1h 56m

Chicago O'Hare Intl

dom. 11/1

6:05 a.m.-11:48 a.m.

1 stop4h 43m

C$ 275

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

jue. 26/2

7:00 a.m.-1:01 p.m.

1 stop7h 01m

Chicago O'Hare Intl

lun. 2/3

12:50 p.m.-3:57 p.m.

Nonstop2h 07m

C$ 297

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Region of Ontario to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Region of Ontario averaging around C$ 315.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 629. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,085. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the evening is the cheapest time of day to fly from Region of Ontario to Chicago when you can find flight prices for as low as C$ 634. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,090 per ticket.

What is the cheapest Ontario to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Ontario - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Region of Ontario when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 411 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Region of Ontario for as low as C$ 273 on momondo.

What cabin class options are available on Ontario to Chicago flights?

There are 4 cabin classes available to choose from on Ontario to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Region of Ontario to Chicago flights?

No. A direct flight is the cheapest option for a flight between Region of Ontario to Chicago.

Cheap Region of Ontario to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago

Best price found	C$ 197
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Region of Ontario in the past 72 hours is C$ 197. The best round-trip flight deal from Region of Ontario to Chicago found on momondo in the last 72 hours is C$ 346.

The fastest flight from Region of Ontario to Chicago takes 1h 50m

Direct flights go from Region of Ontario to Chicago every day.

There is 1 airport near Chicago: Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Ontario to Chicago?
Prices for flights from Ontario to Chicago were last updated today.
How many operators does momondo search for flights from Ontario to Chicago?
There are 5 operators available for flights from Ontario to Chicago as of November 2025.
How old do you have to be to fly from Ontario to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ontario to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Region of Ontario to Chicago?
Based on momondo bookings for flights between Region of Ontario and Chicago, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 16.62% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 13.52%, Boeing 737 MAX 8 with 9.84%, and Boeing 737-800 with 9.58%.

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom C$ 198	Free Cancellation	Rating 8.0 393 reviews	Search Porter Airlines flights
American Airlines	PriceFrom C$ 264	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
Air Canada	PriceFrom C$ 265	Free Cancellation	Rating 7.1 10,462 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 283	Free Cancellation	Rating 7.4 9,027 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 374	Free Cancellation	Rating 7.2 3,168 reviews	Search WestJet flights

Munster

Hammond

Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Ontario to Chicago?

Finding the right flight to Chicago from Ontario is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Ontario to Chicago with flexible booking policies on momondo?

Flights from Ontario to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Ontario to Chicago?

Once all potential Ontario to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Ontario and alert you when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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1 adult

sáb. 20/12

sáb. 27/12

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Popular Cities in the United States

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Flights to Dallasfrom C$ 258

Cheap flights from Ontario to Chicago from C$ 170

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Ontario to Chicago departing on 13/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

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Find the cheapest flights from Ontario to Chicago

Cheap round-trip flights

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Cheap last-minute flights

Cheap direct flights

American Airlines flights from Region of Ontario to Chicago

Our best American Airlines deals on Region of Ontario to Chicago flight tickets

Air Canada flights from Region of Ontario to Chicago

Our best Air Canada deals on Region of Ontario to Chicago flight tickets

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Use the filters below to find and compare flights from Ontario to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Region of Ontario to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Region of Ontario averaging around C$ 315.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Ontario to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Ontario - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Ontario to Chicago flights?

There are 4 cabin classes available to choose from on Ontario to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Region of Ontario to Chicago flights?

No. A direct flight is the cheapest option for a flight between Region of Ontario to Chicago.

What is the cheapest airline that flies from Ontario to Chicago?

Porter Airlines, Air Canada, and American Airlines are the most popular carriers operating from Ontario to Chicago

Which airlines fly to Chicago?

How many flights depart from Region of Ontario to Chicago on average per day?

87 flights are operational daily from Region of Ontario to Chicago as of November 2025. The most popular departure time for this route is 11:00a.m., with 48% of flights per day taking off at noon.

How many flights depart from Region of Ontario to Chicago on average per week?

612 flights are operational weekly from Region of Ontario to Chicago as of November 2025. The most popular departure day for this route is Thu, with 16% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Cheap Region of Ontario to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago

Best price found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Ontario to Chicago?

How many operators does momondo search for flights from Ontario to Chicago?

How old do you have to be to fly from Ontario to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Region of Ontario to Chicago?

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Travelling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Ontario to Chicago?

Can I find flights from Ontario to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Ontario to Chicago?

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago